Reactivity of an N,N-Chelated Germylene Toward Substituted Alkynes, Alkenes, and Allenes
Identifikátory výsledku
Kód výsledku v IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F19%3A39915101" target="_blank" >RIV/00216275:25310/19:39915101 - isvavai.cz</a>
Nalezeny alternativní kódy
RIV/00216208:11310/19:10396152
Výsledek na webu
<a href="https://onlinelibrary.wiley.com/doi/full/10.1002/zaac.201800489" target="_blank" >https://onlinelibrary.wiley.com/doi/full/10.1002/zaac.201800489</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/zaac.201800489" target="_blank" >10.1002/zaac.201800489</a>
Alternativní jazyky
Jazyk výsledku
angličtina
Název v původním jazyce
Reactivity of an N,N-Chelated Germylene Toward Substituted Alkynes, Alkenes, and Allenes
Popis výsledku v původním jazyce
Treatment of N,N-chelated germylene [(iPr)(2)NB(N-2,6-Me2C6H3)(2)]Ge (1) with ferrocenyl alkynes containing carbonyl functionalities, FcC equivalent to CC(O)R, resulted in [2+2+2] cyclization and formation of the respective ferrocenylated 3-Fc-4-C(O)R-1,2-digermacyclobut-3-enes 2-4 [R = Me (2), OEt (3) and NMe2 (4)] bearing intact carbonyl substituents. In contrast, the reaction between 1 and PhC(O)C equivalent to CC(O)Ph led to activation of both C equivalent to C and C=O bonds producing bicyclic compound containing two five-membered 1-germa-2-oxacyclopent-3-ene rings sharing one C-C bond, 4,8-diphenyl-3,7-dioxa-2,6-digermabicyclo[3.3.0]octa-4,8-diene (5). With N-methylmaleimide containing an analogous C(O)CH=CHC(O) fragment, germylene 1 reacted under [2+2+2] cyclization involving the C=C double bond, producing 1,2-digermacyclobutane 6 with unchanged carbonyl moieties. Finally, 1 selectively added to the terminal double bond in allenes CH2=C=CRR ' giving rise to 3-(=CRR ')-1,2-digermacyclobutanes [R/R ' = Me/Me (7), H/OMe (8)] bearing an exo-C=C double bond. All compounds were characterized by H-1, C-13{H-1} NMR, IR and Raman spectroscopy and the molecular structures of 3, 4, 5, and 8 were established by single-crystal X-ray diffraction analysis. The redox behavior of ferrocenylated derivatives 2-4 was studied by cyclic voltammetry.
Název v anglickém jazyce
Reactivity of an N,N-Chelated Germylene Toward Substituted Alkynes, Alkenes, and Allenes
Popis výsledku anglicky
Treatment of N,N-chelated germylene [(iPr)(2)NB(N-2,6-Me2C6H3)(2)]Ge (1) with ferrocenyl alkynes containing carbonyl functionalities, FcC equivalent to CC(O)R, resulted in [2+2+2] cyclization and formation of the respective ferrocenylated 3-Fc-4-C(O)R-1,2-digermacyclobut-3-enes 2-4 [R = Me (2), OEt (3) and NMe2 (4)] bearing intact carbonyl substituents. In contrast, the reaction between 1 and PhC(O)C equivalent to CC(O)Ph led to activation of both C equivalent to C and C=O bonds producing bicyclic compound containing two five-membered 1-germa-2-oxacyclopent-3-ene rings sharing one C-C bond, 4,8-diphenyl-3,7-dioxa-2,6-digermabicyclo[3.3.0]octa-4,8-diene (5). With N-methylmaleimide containing an analogous C(O)CH=CHC(O) fragment, germylene 1 reacted under [2+2+2] cyclization involving the C=C double bond, producing 1,2-digermacyclobutane 6 with unchanged carbonyl moieties. Finally, 1 selectively added to the terminal double bond in allenes CH2=C=CRR ' giving rise to 3-(=CRR ')-1,2-digermacyclobutanes [R/R ' = Me/Me (7), H/OMe (8)] bearing an exo-C=C double bond. All compounds were characterized by H-1, C-13{H-1} NMR, IR and Raman spectroscopy and the molecular structures of 3, 4, 5, and 8 were established by single-crystal X-ray diffraction analysis. The redox behavior of ferrocenylated derivatives 2-4 was studied by cyclic voltammetry.
Klasifikace
Druh
J<sub>imp</sub> - Článek v periodiku v databázi Web of Science
CEP obor
—
OECD FORD obor
10402 - Inorganic and nuclear chemistry
Návaznosti výsledku
Projekt
<a href="/cs/project/GA17-10377S" target="_blank" >GA17-10377S: Multideprotonovatelné, ambifilické a hybridní ligandy s uspořádáním vhodným pro tvorbu oligometalických komplexů kovů</a><br>
Návaznosti
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Ostatní
Rok uplatnění
2019
Kód důvěrnosti údajů
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Údaje specifické pro druh výsledku
Název periodika
Zeitschrift für anorganische und allgemeine Chemie
ISSN
0044-2313
e-ISSN
—
Svazek periodika
645
Číslo periodika v rámci svazku
9
Stát vydavatele periodika
DE - Spolková republika Německo
Počet stran výsledku
8
Strana od-do
671-678
Kód UT WoS článku
000476950200002
EID výsledku v databázi Scopus
—